1,5-Di(4-toluenesulfonamido)-3,7-bismethylenediazacyclooctane → 1,5-Dimethyl-3,7-diazabicyclooctane

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Reaction Steps

A suspension of 1,5-di(4-toluenesulfonamido)-3,7-bismethylenediazacyclooctane 1a (2.22 g, 4.98 mmol) in tetrahydrofuran (75 mL) containing lithium aluminum hydride (1.90 g, 50 mmol) was stirred under a nitrogen atmosphere for 42 h. The reaction mixture was quenched by the dropwise addition of 20% sodium hydroxide solution (4.5 mL) with external cooling. Stirring was continued at room temperature for 3 h and the white granular precipitate that formed was removed by filtration and washed with anhydrous ether (3×50 mL). The combined organic extracts were concentrated on a rotary evaporator to give 0.574 g (82%) of 5 as a colorless solid, mp XX° C. 1H NMR (CDCl3) δ0.99 (s, 6H), δ2.71 (d, J=11.2 Hz, 4H), δ2.92 (d, J=11.2 Hz, 4H), δ2.61 (s, 2H. br); 13C NMR (CDCl3) δ20.4, δ51.7, δ62.6. LRMS (EI) calc. for C8H16N2 140.1; found m/z, 140. Treatment of an ethanolic solution of 5 with picric acid afforded the picrate as a yellow solid, mp 258° C.

Provenance & Evidence